Transcript Hydrocarbon Derivatives - AHS-SCH4U

Hydrocarbon Derivatives
-Alcohols
-Haloalkanes
-Aldehydes
-Ketones
-Carboxylic Acids
-Esters
-Ethers
-Amines
-Amides
Hydrocarbon Derivatives
• These are organic compounds that are based
on hydrocarbons with the addition of
specific functional groups
• A functional group is a reactive group of
atoms (eg. –OH)
• Due to the reactivity of the functional
groups, we can determine the physical and
chemical properties of compounds
• We also classify compounds based on these
groups
• We will now explore six groups of
hydrocarbon derivatives
ALCOHOLS
Alcohols
• An organic compound containing the
hydroxyl, –OH, functional group
• Have the general formula of R—OH
• The “R” represents the alkyl group
• Example:
CH3—CH2—OH
Naming Rules
1. Locate the longest carbon chain (must contain the carbon
attached to the –OH group.) Name the parent alkane
2. The suffix is –ol; indicate the position of the –OH group in
front of the suffix
3. More than one –OH group; use di, tri, tetra and keep entire
root name
4. Number the chain so that the –OH group has the lowest
number
5. Add a position number before the name of the root to indicate
the position of the –OH group
6. Name and number any branches (as you would for alkanes)
7. Put it all together: branches + root
Try it!
• Name this alcohol:
CH3—CH2—CH2—OH
CH3—CH—CH2—CH2—CH3
|
OH
One more...
• Name this alcohol and state whether it is
primary, secondary or tertiary.
CH3—CH—CH2—CH2—CH3
|
OH
Draw:
3,4-dimethylhexan-2-ol
Butane-1,3-diol
Three classes of Alcohols
• Primary Alcohol (1°) – the OH group is
bonded to a carbon that is only bonded to one
other carbon
• Secondary Alcohol (2°)– the OH group is
bonded to a carbon that is bonded to two other
carbon atoms
• Tertiary Alcohol (3°)– the OH group is
bonded to a carbon that is bonded to three
other carbon atoms
Physical properties of alcohols
• Polar or non-polar?
• Boiling points? Intermolecular forces?
Haloalkanes
• HCs with at least one halogen atom
• Basic structure R-X, where R is the root and
X can be F, Cl, Br, I
• Often result of substitution reactions
• Eg. Chloroform, CFCs (refrigerants &
propellants)
Naming haloalkanes
1. Identify the root – longest continuous chain
2. Identify the suffix – which family
3. Type of halogen (F-fluoro, Cl-chloro, Br-bromo,
I-iodo); more than one – di, tri, etc
4. Halogen gets the lowest number
5. Then look for alkyl groups
6. .Halogen substituent groups and alkyl side
groups are arranged alphabetically
Try these…
• CH3-CH2-CH2-Cl
• CH2=CH-CH2-Br
• Try #85-95 on page 49
Physical properties
• polarity/solubility in water?
• Boiling points?
ALDEHYDES
Aldehyde
• Contain a formyl group,
which is a carbonyl functional
group >C=O with a H bonded
to the C atom
Only one possible position – always C#1
• Have characteristic scents and tastes
• Example – Cinnamon or Formaldehyde, vanillin,
cilantro
Naming Aldehydes
• As with other naming (ID root)
• The carbonyl group will always be on a
terminal carbon, thus there is no need to
give a position number
• Simply name the carbon chain; drop the
–e from the end and add –al; give the
C=O position 1
• Add branches (if any) as you have for all
others!
Try Some
O
||
HC—CH2—CH2—CH3
O
||
CH3—CH2—CH—CH
|
CH2—CH3
Try page 52: #96-105
Physical properties of aldehydes
• Polarity?
• Boiling points? Compared to alcohols?
KETONES
Ketones
• Contain the carbonyl group C=O
• Has an alkyl group on either side of the C=O
• General formula R-CO-R`
Naming Ketones
• Find the longest carbon chain containing
C=O
• Number the chain so that C=O has lowest
number
• Drop the final –e from the alkane name and
add –one
• Name and add branches as you would for
alkanes
Try These
O
||
CH3—CH2—CH2—C—CH3
O
||
CH3—CH—C—CH2—CH2—CH3
|
CH3
CARBOXYLIC ACIDS
Carboxylic Acids
• Contain a carboxyl group
O
||
—C—OH
• General formula of R—COOH
• Polar molecules
• Soluble in water
• Have high MP and BP
Naming Carboxylic Acids
• Name the parent alkane; drop the –e at the
end of the alkane name and add –oic acid
• Carboxyl group is always given position
one (no need to state this!)
• Name any branches as we do for alkanes
Try some
O
||
CH3—C—OH
O
||
CH3—CH—CH2—C—OH
|
CH3
ESTERS
Esters
• Derivatives of carboxylic acids
• Contains the functional group
O
||
—C—O—
• General formula RCOOR`
O
• Example:
||
CH3—CH2—C—O—CH3
Naming Esters
• Choose the main part of the ester, containing
the C=O group. Name this as the parent acid.
• Replace the –oic acid with –oate
• Name the second part of the ester as an alkyl
group
• Put them together – alkyl group + parent acid
O
||
CH3—CH2—C—O—CH3
Parent acid
We would name this
Alkyl Group
methyl propanoate
Try One
O
||
CH3—CH2—CH2—CH2—C—O—CH2—CH3
ETHER
Ethers
• An organic compound that has two alkyl
groups joined by an oxygen atom
• Has the general formula of R—O—R`
• R and R` indicate two alkyl groups
• The can be the same or different
• Example:
CH3—CH2—O—CH3
How do we get to this?
• You can think of alcohols and ethers as
derivatives of water!
H—O—H
R—O—H
R—O—R`
Water
Alcohol
Ether
Rules for naming
Common Names
1. List the alkyl groups that are attached to
the oxygen atom, in order of increasing
length.
2. Place the suffix –ether at the end of the
name
No numbers are needed to show the location
of the oxygen atom!
Try it!
Name these ethers
CH3—CH2—O—CH2—CH2
CH3—CH2—CH2—CH2—O—CH2—CH3